These are preliminary reports that have not been peer-reviewed. They should not be regarded as conclusive, guide clinical practice/health-related behavior, or be reported in news media as established information. For more information, please see our FAQs.
3 files

Cycloisomerization of Olefins in Water

submitted on 13.03.2020, 03:21 and posted on 13.03.2020, 13:11 by Jeishla Melendez Matos, Samantha Green, Yuge Chun, Vuong Q. Dang, Russell G. Dushin, Paul Richardson, Jason Chen, David W. Piotrowski, Brian Paegel, Ryan Shenvi
Preparative chemical reactions that occur efficiently under dilute, buffered, aqueous conditions in the presence of biomolecules find application in ligation, peptide synthesis, polynucleotide synthesis and sequencing. However, the identification of functional groups or reagents that are mutually reactive with one another, but unreactive with biopolymers and water, is challenging. Here we show that cobalt catalysts will react with the alkenes of unsaturated tertiary amines under dilute, aqueous, buffered conditions and promote efficient cycloisomerization, in many cases mediating a formal Friedel-Crafts reaction. We find the constraining conditions of biorthogonal chemistry to be beneficial for reaction efficiency as we obtain superior conversion at low catalyst concentration and maintain competent rates in dilute conditions. The efficiency at high dilution in the presence of buffer and nucleobases suggests that these conditions may find use on or in the presence of biomolecules.


NIH R35 GM122606


Email Address of Submitting Author


Scripps Research


United States

ORCID For Submitting Author


Declaration of Conflict of Interest

No conflict of interest

Usage metrics